diff --git a/libs/ui/KisMainWindow.cpp b/libs/ui/KisMainWindow.cpp
--- a/libs/ui/KisMainWindow.cpp
+++ b/libs/ui/KisMainWindow.cpp
@@ -2116,9 +2116,12 @@
     QMenu *docMenu = d->documentMenu->menu();
     docMenu->clear();
 
+    QFontMetrics fontMetrics = docMenu->fontMetrics();
+    int fileStringWidth = int(QApplication::desktop()->screenGeometry(this).width() * .45f);
+
     Q_FOREACH (QPointer<KisDocument> doc, KisPart::instance()->documents()) {
         if (doc) {
-            QString title = doc->url().toDisplayString();
+            QString title = fontMetrics.elidedText(doc->url().toDisplayString(QUrl::PreferLocalFile), Qt::ElideMiddle, fileStringWidth);
             if (title.isEmpty() && doc->image()) {
                 title = doc->image()->objectName();
             }
@@ -2216,10 +2219,10 @@
         if (child && child->document()) {
             QString text;
             if (i < 9) {
-                text = i18n("&%1 %2", i + 1, child->document()->url().toDisplayString());
+                text = i18n("&%1 %2", i + 1, fontMetrics.elidedText(child->document()->url().toDisplayString(QUrl::PreferLocalFile), Qt::ElideMiddle, fileStringWidth));
             }
             else {
-                text = i18n("%1 %2", i + 1, child->document()->url().toDisplayString());
+                text = i18n("%1 %2", i + 1, fontMetrics.elidedText(child->document()->url().toDisplayString(QUrl::PreferLocalFile), Qt::ElideMiddle, fileStringWidth));
             }
 
             QAction *action  = menu->addAction(text);